Compounds of the general Formula I, infra, wherein R.sub.3 is hydrogen are prepared by methods available in the chemical literature (e.g., methods described in the references given below) to couple p-aminobenzamides with a 4-chloroquinoline in a lower alkanol such as ethanol using as catalyst one equivalent of hydrochloric acid. The p-aminobenzamides are derived from the corresponding p-nitrobenzamides by catalytic hydrogenation; the p-nitrobenzamides being prepared from the corresponding amines or ammonia and p-nitrobenzoyl chloride.
Compounds of the general Formula I, infra, wherein R.sub.3 is alkyl are prepared by treating a compound wherein R.sub.3 is hydrogen with the corresponding alkyl halide, e.g., methyl iodide or bromide and an alkali metal hydride or alkali metal amide, e.g., sodium hydride or sodium amide.
M. H. Fukami, Amides of 4-Quinolylaminoacids as Chemotherapeutic Agents, University of Michigan, Ph.D. Thesis 1967, describes 1-[p-[(7-chloro-4-quinolyl)amino]-N,N-(3-methyl-3-azapentamethylene]benzam ide and its meta isomer. Slight activity against Schistosoma Mansoni cercariae in mice and against Plasmodium berghei at a dose of 160 mg./kg. subcutaneously to mice are disclosed.